Luteolin

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Luteolin
The chemical structure of luteolin
Identifiers
CAS number491-70-3 YesY
PubChem5280445
ChemSpider4444102 N
UNIIKUX1ZNC9J2 N
ChEBICHEBI:15864 N
ChEMBLCHEMBL151 N
Jmol-3D imagesImage 1
Properties
Molecular formulaC15H10O6
Molar mass286.24 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
 
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Luteolin
The chemical structure of luteolin
Identifiers
CAS number491-70-3 YesY
PubChem5280445
ChemSpider4444102 N
UNIIKUX1ZNC9J2 N
ChEBICHEBI:15864 N
ChEMBLCHEMBL151 N
Jmol-3D imagesImage 1
Properties
Molecular formulaC15H10O6
Molar mass286.24 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Luteolin is a flavone, a type of flavonoid. Like all flavonoids, it has a yellow crystalline appearance.[1]

Natural occurrences[edit]

Luteolin can be found in Terminalia chebula. It is most often found in leaves, but it is also seen in rinds, barks, clover blossom, and ragweed pollen.[1] It has also been isolated from Salvia tomentosa.[2]

Dietary sources include celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano.[3][4] It can also be found in the seeds of the palm Aiphanes aculeata.[5]

Metabolism[edit]

These enzymes are part of luteolin metabolism:

Glycosides[edit]

Biomedical research[edit]

Luteolin has been studied in several preliminary in vitro scientific investigations. Proposed activities include antioxidant activity (ie. scavenging of free radicals), promotion of carbohydrate metabolism, and immune system modulation.[citation needed] Other in vitro studies suggest luteolin has anti-inflammatory activity,[7][8] and that it acts as a monoamine transporter activator,[9] a phosphodiesterase inhibitor,[10] and an interleukin 6 inhibitor.[7] In vivo studies show luteolin affects xylazine/ketamine-induced anesthesia in mice.[11] In vitro and in vivo experiments also suggest luteolin may inhibit the development of skin cancer.[12][13] Importantly, the therapeutic value of the above findings is unclear, and will remain so until further detailed in vivo, toxicity, and clinical studies are performed.

Adverse effects[edit]

Gastrointestinal adverse effects, such as nausea, vomiting, and gastric hypersecretion, may occur.[citation needed] Luteolin has also recently been found to have adverse effects in in vitro research with endometrial cancer cells.[14]

References[edit]

  1. ^ a b Mann, John (1992). Secondary Metabolism (2nd ed.). Oxford, UK: Oxford University Press. pp. 279–280. ISBN 0-19-855529-6. 
  2. ^ A. Ulubelen, M. Miski, P. Neuman, and T. J. Mabry (1979). "Flavonoids of Salvia tomentosa (Labiatae)". Journal of Natural Products 42 (4): 261–3. doi:10.1021/np50003a002. 
  3. ^ Kayoko Shimoi, Hisae Okada, Michiyo Furugori, Toshinao Goda, Sachiko Takase, Masayuki Suzuki, Yukihiko Hara, Hiroyo Yamamoto, Naohide Kinae (1998). "Intestinal absorption of luteolin and luteolin 7-O-[beta]-glucoside in rats and humans". FEBS Letters 438 (3): 220–4. doi:10.1016/S0014-5793(98)01304-0. PMID 9827549. 
  4. ^ López-Lázaro M. (2009). "Distribution and biological activities of the flavonoid luteolin". Mini Rev Med Chem. 9 (1): 31–59. doi:10.2174/138955709787001712. PMID 19149659. 
  5. ^ Lee, D; Cuendet, M; Vigo, JS; Graham, JG; Cabieses, F; Fong, HH; Pezzuto, JM; Kinghorn, AD (2001). "A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata". Organic Letters 3 (14): 2169–71. doi:10.1021/ol015985j. PMID 11440571. 
  6. ^ Capanlar, S; Böke, N; Yaşa, I; Kirmizigül, S (2010). "A novel glycoside from Acanthus hirsutus (Acanthaceae)". Natural product communications 5 (4): 563–6. PMID 20433073. 
  7. ^ a b Johnson; Kelley, KW; Johnson, RW (May 2008). "Luteolin reduces IL-6 production in microglia by inhibiting JNK phosphorylation and activation of AP-1". Proc. Natl. Acad. Sci. U.S.A. 105 (21): 7534–9. doi:10.1073/pnas.0802865105. PMC 2396685. PMID 18490655. 
  8. ^ Theoharides (2009). "Luteolin as a Therapeutic Option for Multiple Sclerosis". Journal of Neuroinflammation 6 (1): 29. doi:10.1186/1742-2094-6-29. PMC 2768692. PMID 19825165. 
  9. ^ Zhao, G; Qin, GW; Wang, J; Chu, WJ; Guo, LH (2010). "Functional activation of monoamine transporters by luteolin and apigenin isolated from the fruit of Perilla frutescens (L.) Britt". Neurochemistry international 56 (1): 168–76. doi:10.1016/j.neuint.2009.09.015. PMID 19815045. 
  10. ^ Yu MC, Chen JH, Lai CY, Han CY, Ko WC (February 2010). "Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1-5, displaced [3H]-rolipram from high-affinity only rolipram-binding sites and reversed xylazine/ketamine-induced anesthesia". Eur. J. Pharmacol. 627 (1–3): 269–75. doi:10.1016/j.ejphar.2009.10.031. PMID 19853596. 
  11. ^ Yu, MC; Chen, JH; Lai, CY; Han, CY; Ko, WC (2010). "Luteolin, a non-selective competitive inhibitor of phosphodiesterases 1-5, displaced 3H-rolipram from high-affinity rolipram-binding sites and reversed xylazine/ketamine-induced anesthesia". European Journal of Pharmacology 627 (1–3): 269–75. doi:10.1016/j.ejphar.2009.10.031. PMID 19853596. 
  12. ^ Byun, Sanguine; KW Lee, SK Jung, EJ Lee, MK Hwang,SH Lim, AM Bode, HJ Lee,Z Dong (2010). "Luteolin Inhibits Protein Kinase Cε and c-Src Activities and UVB-Induced Skin Cancer". Cancer Research 70 (6): 2415–23. doi:10.1158/0008-5472.CAN-09-4093. PMID 20215519. 
  13. ^ López-Lázaro M. (2009). "Distribution and biological activities of the flavonoid luteolin". Mini Rev Med Chem 9 (1): 31–59. doi:10.2174/138955709787001712. PMID 19149659. 
  14. ^ "Common Autism Supplement Affects Endocrine System". Science Daily. July 15, 2013. Retrieved 2 September 2013.